openssh_keypair: Adding passphrase parameter (#225)

* Integrating openssh module utils with openssh_keypair

* Added explicit PEM formatting for OpenSSH < 7.8

* Adding changelog fragment

* Adding OpenSSL/cryptography dependency for integration tests

* Adding private_key_format option and removing forced cryptography update for CI

* Fixed version check for bcrypt and key_format option name

* Setting no_log=False for private_key_format

* Docs correction and simplification of control flow for private_key_format

changelogs/fragments/225-openssh-keypair-passphrase.yml

@@ -0,0 +1,2 @@
+minor_changes:
+  - openssh_keypair - Added ``passphrase`` paramter to openssh_keypair for encrypting/decrtypting OpenSSH private keys (https://github.com/ansible-collections/community.crypto/pull/225).

plugins/module_utils/openssh/cryptography_openssh.py

@@ -19,24 +19,23 @@ from __future__ import absolute_import, division, print_function
 __metaclass__ = type
 
 from base64 import b64encode, b64decode
+from distutils.version import LooseVersion
 from getpass import getuser
 from socket import gethostname
 
-from ansible_collections.community.crypto.plugins.module_utils.crypto.basic import (
-    HAS_CRYPTOGRAPHY,
-    CRYPTOGRAPHY_HAS_ED25519,
-)
-
 try:
+    import cryptography as c
     from cryptography.exceptions import InvalidSignature, UnsupportedAlgorithm
     from cryptography.hazmat.backends.openssl import backend
     from cryptography.hazmat.primitives import hashes, serialization
     from cryptography.hazmat.primitives.asymmetric import dsa, ec, rsa, padding
     from cryptography.hazmat.primitives.asymmetric.ed25519 import Ed25519PrivateKey, Ed25519PublicKey
-except ImportError:
-    pass
 
-if HAS_CRYPTOGRAPHY and CRYPTOGRAPHY_HAS_ED25519:
+    if LooseVersion(c.__version__) >= LooseVersion("3.0"):
+        HAS_OPENSSH_PRIVATE_FORMAT = True
+    else:
+        HAS_OPENSSH_PRIVATE_FORMAT = False
+
     HAS_OPENSSH_SUPPORT = True
 
     _ALGORITHM_PARAMETERS = {
@@ -76,7 +75,8 @@ if HAS_CRYPTOGRAPHY and CRYPTOGRAPHY_HAS_ED25519:
             }
         }
     }
-else:
+except ImportError:
+    HAS_OPENSSH_PRIVATE_FORMAT = False
     HAS_OPENSSH_SUPPORT = False
     _ALGORITHM_PARAMETERS = {}
 
@@ -192,12 +192,14 @@ class Asymmetric_Keypair(object):
         )
 
     @classmethod
-    def load(cls, path, passphrase=None, key_format='PEM'):
+    def load(cls, path, passphrase=None, private_key_format='PEM', public_key_format='PEM', no_public_key=False):
         """Returns an Asymmetric_Keypair object loaded from the supplied file path
 
            :path: A path to an existing private key to be loaded
            :passphrase: Secret of type bytes used to decrypt the private key being loaded
-           :key_format: Format of key files to be loaded
+           :private_key_format: Format of private key to be loaded
+           :public_key_format: Format of public key to be loaded
+           :no_public_key: Set 'True' to only load a private key and automatically populate the matching public key
         """
 
         if passphrase:
@@ -205,8 +207,11 @@ class Asymmetric_Keypair(object):
         else:
             encryption_algorithm = serialization.NoEncryption()
 
-        privatekey = load_privatekey(path, passphrase, key_format)
-        publickey = load_publickey(path + '.pub', key_format)
+        privatekey = load_privatekey(path, passphrase, private_key_format)
+        if no_public_key:
+            publickey = privatekey.public_key()
+        else:
+            publickey = load_publickey(path + '.pub', public_key_format)
 
         # Ed25519 keys are always of size 256 and do not have a key_size attribute
         if isinstance(privatekey, Ed25519PrivateKey):
@@ -352,11 +357,11 @@ class OpenSSH_Keypair(object):
            :comment: Comment for a newly generated OpenSSH public key
         """
 
-        if not comment:
+        if comment is None:
             comment = "%s@%s" % (getuser(), gethostname())
 
         asym_keypair = Asymmetric_Keypair.generate(keytype, size, passphrase)
-        openssh_privatekey = cls.encode_openssh_privatekey(asym_keypair)
+        openssh_privatekey = cls.encode_openssh_privatekey(asym_keypair, 'SSH')
         openssh_publickey = cls.encode_openssh_publickey(asym_keypair, comment)
         fingerprint = calculate_fingerprint(openssh_publickey)
 
@@ -365,20 +370,21 @@ class OpenSSH_Keypair(object):
             openssh_privatekey=openssh_privatekey,
             openssh_publickey=openssh_publickey,
             fingerprint=fingerprint,
-            comment=comment
+            comment=comment,
         )
 
     @classmethod
-    def load(cls, path, passphrase=None):
+    def load(cls, path, passphrase=None, no_public_key=False):
         """Returns an Openssh_Keypair object loaded from the supplied file path
 
            :path: A path to an existing private key to be loaded
            :passphrase: Secret used to decrypt the private key being loaded
+           :no_public_key: Set 'True' to only load a private key and automatically populate the matching public key
         """
 
         comment = extract_comment(path + '.pub')
-        asym_keypair = Asymmetric_Keypair.load(path, passphrase, 'SSH')
-        openssh_privatekey = cls.encode_openssh_privatekey(asym_keypair)
+        asym_keypair = Asymmetric_Keypair.load(path, passphrase, 'SSH', 'SSH', no_public_key)
+        openssh_privatekey = cls.encode_openssh_privatekey(asym_keypair, 'SSH')
         openssh_publickey = cls.encode_openssh_publickey(asym_keypair, comment)
         fingerprint = calculate_fingerprint(openssh_publickey)
 
@@ -387,21 +393,31 @@ class OpenSSH_Keypair(object):
             openssh_privatekey=openssh_privatekey,
             openssh_publickey=openssh_publickey,
             fingerprint=fingerprint,
-            comment=comment
+            comment=comment,
         )
 
     @staticmethod
-    def encode_openssh_privatekey(asym_keypair):
+    def encode_openssh_privatekey(asym_keypair, key_format):
         """Returns an OpenSSH encoded private key for a given keypair
 
            :asym_keypair: Asymmetric_Keypair from the private key is extracted
+           :key_format: Format of the encoded private key.
         """
 
-        # OpenSSH formatted private keys are not available in Cryptography <3.0
-        try:
-            privatekey_format = serialization.PrivateFormat.OpenSSH
-        except AttributeError:
+        if key_format == 'SSH':
+            # Default to PEM format if SSH not available
+            if not HAS_OPENSSH_PRIVATE_FORMAT:
+                privatekey_format = serialization.PrivateFormat.PKCS8
+            else:
+                privatekey_format = serialization.PrivateFormat.OpenSSH
+        elif key_format == 'PKCS8':
             privatekey_format = serialization.PrivateFormat.PKCS8
+        elif key_format == 'PKCS1':
+            if asym_keypair.key_type == 'ed25519':
+                raise InvalidKeyFormatError("ed25519 keys cannot be represented in PKCS1 format")
+            privatekey_format = serialization.PrivateFormat.TraditionalOpenSSL
+        else:
+            raise InvalidKeyFormatError("The accepted private key formats are SSH, PKCS8, and PKCS1")
 
         encoded_privatekey = asym_keypair.private_key.private_bytes(
             encoding=serialization.Encoding.PEM,
@@ -425,7 +441,7 @@ class OpenSSH_Keypair(object):
 
         validate_comment(comment)
 
-        encoded_publickey += (" %s" % comment).encode(encoding=_TEXT_ENCODING)
+        encoded_publickey += (" %s" % comment).encode(encoding=_TEXT_ENCODING) if comment else b''
 
         return encoded_publickey
 
@@ -502,7 +518,7 @@ class OpenSSH_Keypair(object):
         validate_comment(comment)
 
         self.__comment = comment
-        encoded_comment = (" %s" % self.__comment).encode(encoding=_TEXT_ENCODING)
+        encoded_comment = (" %s" % self.__comment).encode(encoding=_TEXT_ENCODING) if self.__comment else b''
         self.__openssh_publickey = b' '.join(self.__openssh_publickey.split(b' ', 2)[:2]) + encoded_comment
         return self.__openssh_publickey
 
@@ -513,7 +529,7 @@ class OpenSSH_Keypair(object):
         """
 
         self.__asym_keypair.update_passphrase(passphrase)
-        self.__openssh_privatekey = OpenSSH_Keypair.encode_openssh_privatekey(self.__asym_keypair)
+        self.__openssh_privatekey = OpenSSH_Keypair.encode_openssh_privatekey(self.__asym_keypair, 'SSH')
 
 
 def load_privatekey(path, passphrase, key_format):
@@ -549,7 +565,22 @@ def load_privatekey(path, passphrase, key_format):
             )
 
     except ValueError as e:
-        raise InvalidPrivateKeyFileError(e)
+        # Revert to PEM if key could not be loaded in SSH format
+        if key_format == 'SSH':
+            try:
+                privatekey = privatekey_loaders['PEM'](
+                    data=content,
+                    password=passphrase,
+                    backend=backend,
+                )
+            except ValueError as e:
+                raise InvalidPrivateKeyFileError(e)
+            except TypeError as e:
+                raise InvalidPassphraseError(e)
+            except UnsupportedAlgorithm as e:
+                raise InvalidAlgorithmError(e)
+        else:
+            raise InvalidPrivateKeyFileError(e)
     except TypeError as e:
         raise InvalidPassphraseError(e)
     except UnsupportedAlgorithm as e:
@@ -645,4 +676,4 @@ def calculate_fingerprint(openssh_publickey):
     decoded_pubkey = b64decode(openssh_publickey.split(b' ')[1])
     digest.update(decoded_pubkey)
 
-    return b64encode(digest.finalize()).decode(encoding=_TEXT_ENCODING).rstrip('=')
+    return 'SHA256:%s' % b64encode(digest.finalize()).decode(encoding=_TEXT_ENCODING).rstrip('=')

plugins/modules/openssh_keypair.py

@@ -7,7 +7,6 @@
 from __future__ import absolute_import, division, print_function
 __metaclass__ = type
 
-
 DOCUMENTATION = '''
 ---
 module: openssh_keypair
@@ -19,6 +18,8 @@ description:
       or C(ecdsa) private keys."
 requirements:
     - "ssh-keygen"
+    - cryptography >= 2.6 (if using I(passphrase) and OpenSSH < 7.8 is installed)
+    - cryptography >= 3.0 (if using I(passphrase) and OpenSSH >= 7.8 is installed)
 options:
     state:
         description:
@@ -55,6 +56,23 @@ options:
         description:
             - Provides a new comment to the public key.
         type: str
+    passphrase:
+        description:
+            - Passphrase used to decrypt an existing private key or encrypt a newly generated private key.
+            - Passphrases are not supported for I(type=rsa1).
+        type: str
+        version_added: 1.7.0
+    private_key_format:
+        description:
+            - Used when a value for I(passphrase) is provided to select a format for the private key at the provided I(path).
+            - The only valid option currently is C(auto) which will match the key format of the installed OpenSSH version.
+            - For OpenSSH < 7.8 private keys will be in PKCS1 format except ed25519 keys which will be in OpenSSH format.
+            - For OpenSSH >= 7.8 all private key types will be in the OpenSSH format.
+        type: str
+        default: auto
+        choices:
+            - auto
+        version_added: 1.7.0
     regenerate:
         description:
             - Allows to configure in which situations the module is allowed to regenerate private keys.
@@ -101,6 +119,11 @@ EXAMPLES = '''
   community.crypto.openssh_keypair:
     path: /tmp/id_ssh_rsa
 
+- name: Generate an OpenSSH keypair with the default values (4096 bits, rsa) and encrypted private key
+  community.crypto.openssh_keypair:
+    path: /tmp/id_ssh_rsa
+    passphrase: super_secret_password
+
 - name: Generate an OpenSSH rsa keypair with a different size (2048 bits)
   community.crypto.openssh_keypair:
     path: /tmp/id_ssh_rsa
@@ -153,9 +176,19 @@ comment:
 import errno
 import os
 import stat
+from distutils.version import LooseVersion
 
-from ansible.module_utils.basic import AnsibleModule
-from ansible.module_utils._text import to_native
+from ansible.module_utils.basic import AnsibleModule, missing_required_lib
+from ansible.module_utils._text import to_native, to_text, to_bytes
+
+from ansible_collections.community.crypto.plugins.module_utils.crypto.openssh import parse_openssh_version
+from ansible_collections.community.crypto.plugins.module_utils.openssh.cryptography_openssh import (
+    HAS_OPENSSH_SUPPORT,
+    HAS_OPENSSH_PRIVATE_FORMAT,
+    InvalidPassphraseError,
+    InvalidPrivateKeyFileError,
+    OpenSSH_Keypair,
+)
 
 
 class KeypairError(Exception):
@@ -171,6 +204,7 @@ class Keypair(object):
         self.size = module.params['size']
         self.type = module.params['type']
         self.comment = module.params['comment']
+        self.passphrase = module.params['passphrase']
         self.changed = False
         self.check_mode = module.check_mode
         self.privatekey = None
@@ -180,6 +214,44 @@ class Keypair(object):
         if self.regenerate == 'always':
             self.force = True
 
+        # The empty string is intentionally ignored so that dependency checks do not cause unnecessary failure
+        if self.passphrase:
+            if not HAS_OPENSSH_SUPPORT:
+                module.fail_json(
+                    msg=missing_required_lib(
+                        'cryptography >= 2.6',
+                        reason="to encrypt/decrypt private keys with passphrases"
+                    )
+                )
+
+            if module.params['private_key_format'] == 'auto':
+                ssh = module.get_bin_path('ssh', True)
+                proc = module.run_command([ssh, '-Vq'])
+                ssh_version = parse_openssh_version(proc[2].strip())
+
+                self.private_key_format = 'SSH'
+
+                if LooseVersion(ssh_version) < LooseVersion("7.8") and self.type != 'ed25519':
+                    # OpenSSH made SSH formatted private keys available in version 6.5,
+                    # but still defaulted to PKCS1 format with the exception of ed25519 keys
+                    self.private_key_format = 'PKCS1'
+
+                if self.private_key_format == 'SSH' and not HAS_OPENSSH_PRIVATE_FORMAT:
+                    module.fail_json(
+                        msg=missing_required_lib(
+                            'cryptography >= 3.0',
+                            reason="to load/dump private keys in the default OpenSSH format for OpenSSH >= 7.8 " +
+                                   "or for ed25519 keys"
+                        )
+                    )
+
+            if self.type == 'rsa1':
+                module.fail_json(msg="Passphrases are not supported for RSA1 keys.")
+
+            self.passphrase = to_bytes(self.passphrase)
+        else:
+            self.private_key_format = None
+
         if self.type in ('rsa', 'rsa1'):
             self.size = 4096 if self.size is None else self.size
             if self.size < 1024:
@@ -204,39 +276,71 @@ class Keypair(object):
     def generate(self, module):
         # generate a keypair
         if self.force or not self.isPrivateKeyValid(module, perms_required=False):
-            args = [
-                module.get_bin_path('ssh-keygen', True),
-                '-q',
-                '-N', '',
-                '-b', str(self.size),
-                '-t', self.type,
-                '-f', self.path,
-            ]
-
-            if self.comment:
-                args.extend(['-C', self.comment])
-            else:
-                args.extend(['-C', ""])
-
             try:
                 if os.path.exists(self.path) and not os.access(self.path, os.W_OK):
                     os.chmod(self.path, stat.S_IWUSR + stat.S_IRUSR)
                 self.changed = True
-                stdin_data = None
-                if os.path.exists(self.path):
-                    stdin_data = 'y'
-                module.run_command(args, data=stdin_data)
-                proc = module.run_command([module.get_bin_path('ssh-keygen', True), '-lf', self.path])
-                self.fingerprint = proc[1].split()
-                pubkey = module.run_command([module.get_bin_path('ssh-keygen', True), '-yf', self.path])
-                self.public_key = pubkey[1].strip('\n')
+
+                if not self.passphrase:
+                    args = [
+                        module.get_bin_path('ssh-keygen', True),
+                        '-q',
+                        '-N', '',
+                        '-b', str(self.size),
+                        '-t', self.type,
+                        '-f', self.path,
+                    ]
+
+                    if self.comment:
+                        args.extend(['-C', self.comment])
+                    else:
+                        args.extend(['-C', ""])
+
+                    stdin_data = None
+                    if os.path.exists(self.path):
+                        stdin_data = 'y'
+                    module.run_command(args, data=stdin_data)
+                    proc = module.run_command([module.get_bin_path('ssh-keygen', True), '-lf', self.path])
+                    self.fingerprint = proc[1].split()
+                    pubkey = module.run_command([module.get_bin_path('ssh-keygen', True), '-yf', self.path])
+                    self.public_key = pubkey[1].strip('\n')
+                else:
+                    keypair = OpenSSH_Keypair.generate(
+                        keytype=self.type,
+                        size=self.size,
+                        passphrase=self.passphrase,
+                        comment=self.comment if self.comment else "",
+                    )
+                    with open(self.path, 'w+b') as f:
+                        f.write(
+                            OpenSSH_Keypair.encode_openssh_privatekey(
+                                keypair.asymmetric_keypair,
+                                self.private_key_format
+                            )
+                        )
+                    os.chmod(self.path, stat.S_IWUSR + stat.S_IRUSR)
+                    with open(self.path + '.pub', 'w+b') as f:
+                        f.write(keypair.public_key)
+                    os.chmod(self.path + ".pub", stat.S_IWUSR + stat.S_IRUSR + stat.S_IRGRP + stat.S_IROTH)
+                    self.fingerprint = [
+                        str(keypair.size), keypair.fingerprint, keypair.comment, "(%s)" % keypair.key_type.upper()
+                    ]
+                    self.public_key = to_text(b' '.join(keypair.public_key.split(b' ', 2)[:2]))
             except Exception as e:
                 self.remove()
                 module.fail_json(msg="%s" % to_native(e))
 
         elif not self.isPublicKeyValid(module, perms_required=False):
-            pubkey = module.run_command([module.get_bin_path('ssh-keygen', True), '-yf', self.path])
-            pubkey = pubkey[1].strip('\n')
+            if not self.passphrase:
+                pubkey = module.run_command([module.get_bin_path('ssh-keygen', True), '-yf', self.path])
+                pubkey = pubkey[1].strip('\n')
+            else:
+                keypair = OpenSSH_Keypair.load(
+                    path=self.path,
+                    passphrase=self.passphrase,
+                    no_public_key=True,
+                )
+                pubkey = to_text(keypair.public_key)
             try:
                 self.changed = True
                 with open(self.path + ".pub", "w") as pubkey_f:
@@ -252,9 +356,14 @@ class Keypair(object):
                 try:
                     if os.path.exists(self.path) and not os.access(self.path, os.W_OK):
                         os.chmod(self.path, stat.S_IWUSR + stat.S_IRUSR)
-                    args = [module.get_bin_path('ssh-keygen', True),
-                            '-q', '-o', '-c', '-C', self.comment, '-f', self.path]
-                    module.run_command(args)
+                    if not self.passphrase:
+                        args = [module.get_bin_path('ssh-keygen', True),
+                                '-q', '-o', '-c', '-C', self.comment, '-f', self.path]
+                        module.run_command(args)
+                    else:
+                        keypair.comment = self.comment
+                        with open(self.path + ".pub", "w+b") as pubkey_f:
+                            pubkey_f.write(keypair.public_key + b'\n')
                 except IOError:
                     module.fail_json(
                         msg='Unable to update the comment for the public key.')
@@ -269,11 +378,26 @@ class Keypair(object):
     def _check_pass_protected_or_broken_key(self, module):
         key_state = module.run_command([module.get_bin_path('ssh-keygen', True),
                                         '-P', '', '-yf', self.path], check_rc=False)
-        if key_state[0] == 255 or 'is not a public key file' in key_state[2]:
-            return True
-        if 'incorrect passphrase' in key_state[2] or 'load failed' in key_state[2]:
-            return True
-        return False
+        if not self.passphrase:
+            if key_state[0] == 255 or 'is not a public key file' in key_state[2]:
+                return True
+            if 'incorrect passphrase' in key_state[2] or 'load failed' in key_state[2]:
+                return True
+            return False
+        else:
+            try:
+                OpenSSH_Keypair.load(
+                    path=self.path,
+                    passphrase=self.passphrase,
+                    no_public_key=True,
+                )
+            except (InvalidPrivateKeyFileError, InvalidPassphraseError) as e:
+                return True
+            # Cryptography >= 3.0 uses a SSH key loader which does not raise an exception when a passphrase is provided
+            # when loading an unencrypted key so 'ssh-keygen' is used for this check
+            if key_state[0] == 0:
+                return True
+            return False
 
     def isPrivateKeyValid(self, module, perms_required=True):
 
@@ -365,8 +489,16 @@ class Keypair(object):
 
         pubkey_parts = _parse_pubkey(_get_pubkey_content())
 
-        pubkey = module.run_command([module.get_bin_path('ssh-keygen', True), '-yf', self.path])
-        pubkey = pubkey[1].strip('\n')
+        if not self.passphrase:
+            pubkey = module.run_command([module.get_bin_path('ssh-keygen', True), '-yf', self.path])
+            pubkey = pubkey[1].strip('\n')
+        else:
+            keypair = OpenSSH_Keypair.load(
+                path=self.path,
+                passphrase=self.passphrase,
+                no_public_key=True,
+            )
+            pubkey = to_text(keypair.public_key)
         if _pubkey_valid(pubkey):
             self.public_key = pubkey
         else:
@@ -438,6 +570,8 @@ def main():
                 default='partial_idempotence',
                 choices=['never', 'fail', 'partial_idempotence', 'full_idempotence', 'always']
             ),
+            passphrase=dict(type='str', no_log=True),
+            private_key_format=dict(type='str', default='auto', no_log=False, choices=['auto'])
         ),
         supports_check_mode=True,
         add_file_common_args=True,

tests/integration/targets/openssh_keypair/meta/main.yml

@@ -1,2 +1,3 @@
 dependencies:
   - setup_ssh_keygen
+  - setup_openssl

tests/integration/targets/openssh_keypair/tasks/main.yml

@@ -4,6 +4,9 @@
 # and should not be used as examples of how to write Ansible roles #
 ####################################################################
 
+# Bumps up cryptography and bcrypt versions to be compatible with OpenSSH >= 7.8
+- import_tasks: ./setup_bcrypt.yml
+
 - name: Generate privatekey1 - standard (check mode)
   openssh_keypair:
     path: '{{ output_dir }}/privatekey1'
@@ -124,7 +127,7 @@
   register: privatekey7_modified_result
 
 - name: Generate password protected key
-  command: 'ssh-keygen -f {{ output_dir }}/privatekey8 -N password'
+  command: 'ssh-keygen -f {{ output_dir }}/privatekey8 -N {{ passphrase }}'
 
 - name: Try to modify the password protected key - should fail
   openssh_keypair:
@@ -140,6 +143,58 @@
     size: 2048
   register: privatekey8_result_force
 
+- name: Generate another password protected key
+  command: 'ssh-keygen -f {{ output_dir }}/privatekey9 -N {{ passphrase }}'
+
+- name: Try to modify the password protected key with passphrase
+  openssh_keypair:
+    path: '{{ output_dir }}/privatekey9'
+    size: 1024
+    passphrase: "{{ passphrase }}"
+  register: privatekey9_modified_result
+  when: cryptography_version.stdout is version('3.0', '>=') and bcrypt_version.stdout is version('3.1.5', '>=')
+
+- name: Generate another unprotected key
+  openssh_keypair:
+    path: '{{ output_dir }}/privatekey10'
+    size: 2048
+
+- name: Try to Modify unprotected key with passphrase
+  openssh_keypair:
+    path: '{{ output_dir }}/privatekey10'
+    size: 2048
+    passphrase: "{{ passphrase }}"
+  ignore_errors: true
+  register: privatekey10_result
+  when: cryptography_version.stdout is version('3.0', '>=') and bcrypt_version.stdout is version('3.1.5', '>=')
+
+
+- name: Try to force modify the password protected key with force=true
+  openssh_keypair:
+    path: '{{ output_dir }}/privatekey10'
+    size: 2048
+    passphrase: "{{ passphrase }}"
+    force: true
+  register: privatekey10_result_force
+  when: cryptography_version.stdout is version('3.0', '>=') and bcrypt_version.stdout is version('3.1.5', '>=')
+
+- name: Ensure that ssh-keygen can read keys generated with passphrase
+  command: 'ssh-keygen -yf {{ output_dir }}/privatekey10 -P {{ passphrase }}'
+  register: privatekey10_result_sshkeygen
+  when: cryptography_version.stdout is version('3.0', '>=') and bcrypt_version.stdout is version('3.1.5', '>=')
+
+- name: Generate PEM encoded key with passphrase
+  command: 'ssh-keygen -f {{ output_dir }}/privatekey11 -N {{ passphrase }} -m PEM'
+  when: cryptography_version.stdout is version('3.0', '>=') and bcrypt_version.stdout is version('3.1.5', '>=')
+
+- name: Try to verify a PEM encoded key
+  openssh_keypair:
+    path: '{{ output_dir }}/privatekey11'
+    size: 2048
+    passphrase: "{{ passphrase }}"
+  register: privatekey11_result
+  when: cryptography_version.stdout is version('3.0', '>=') and bcrypt_version.stdout is version('3.1.5', '>=')
+
 - import_tasks: ../tests/validate.yml
 
 
@@ -152,8 +207,9 @@
     size: 1024
   loop: "{{ regenerate_values }}"
 - name: Regenerate - setup password protected keys
-  command: 'ssh-keygen -f {{ output_dir }}/regenerate-b-{{ item }} -N password'
+  command: 'ssh-keygen -f {{ output_dir }}/regenerate-b-{{ item }} -N {{ passphrase }}'
   loop: "{{ regenerate_values }}"
+
 - name: Regenerate - setup broken keys
   copy:
     dest: '{{ output_dir }}/regenerate-c-{{ item.0 }}{{ item.1 }}'
@@ -162,6 +218,10 @@
   with_nested:
     - "{{ regenerate_values }}"
     - [ '', '.pub' ]
+    -
+- name: Regenerate - setup password protected keys for passphrse test
+  command: 'ssh-keygen -f {{ output_dir }}/regenerate-d-{{ item }} -N {{ passphrase }}'
+  loop: "{{ regenerate_values }}"
 
 - name: Regenerate - modify broken keys (check mode)
   openssh_keypair:
@@ -225,6 +285,29 @@
       - result.results[3] is changed
       - result.results[4] is changed
 
+- name: Regenerate - modify password protected keys with passphrase (check mode)
+  openssh_keypair:
+    path: '{{ output_dir }}/regenerate-b-{{ item }}'
+    type: rsa
+    size: 1024
+    passphrase: "{{ passphrase }}"
+    regenerate: '{{ item }}'
+  check_mode: yes
+  loop: "{{ regenerate_values }}"
+  ignore_errors: yes
+  register: result
+  when: cryptography_version.stdout is version('3.0', '>=') and bcrypt_version.stdout is version('3.1.5', '>=')
+
+- assert:
+    that:
+      - result.results[0] is success
+      - result.results[1] is failed
+      - "'Key has wrong type and/or size. Will not proceed.' in result.results[1].msg"
+      - result.results[2] is changed
+      - result.results[3] is changed
+      - result.results[4] is changed
+  when: cryptography_version.stdout is version('3.0', '>=') and bcrypt_version.stdout is version('3.1.5', '>=')
+
 - name: Regenerate - modify password protected keys
   openssh_keypair:
     path: '{{ output_dir }}/regenerate-b-{{ item }}'
@@ -245,6 +328,28 @@
       - result.results[3] is changed
       - result.results[4] is changed
 
+- name: Regenerate - modify password protected keys with passphrase
+  openssh_keypair:
+    path: '{{ output_dir }}/regenerate-d-{{ item }}'
+    type: rsa
+    size: 1024
+    passphrase: "{{ passphrase }}"
+    regenerate: '{{ item }}'
+  loop: "{{ regenerate_values }}"
+  ignore_errors: yes
+  register: result
+  when: cryptography_version.stdout is version('3.0', '>=') and bcrypt_version.stdout is version('3.1.5', '>=')
+
+- assert:
+    that:
+      - result.results[0] is success
+      - result.results[1] is failed
+      - "'Key has wrong type and/or size. Will not proceed.' in result.results[1].msg"
+      - result.results[2] is changed
+      - result.results[3] is changed
+      - result.results[4] is changed
+  when: cryptography_version.stdout is version('3.0', '>=') and bcrypt_version.stdout is version('3.1.5', '>=')
+
 - name: Regenerate - not modify regular keys (check mode)
   openssh_keypair:
     path: '{{ output_dir }}/regenerate-a-{{ item }}'

tests/integration/targets/openssh_keypair/tasks/setup_bcrypt.yml

@@ -0,0 +1,24 @@
+---
+####################################################################
+# WARNING: These are designed specifically for Ansible tests       #
+# and should not be used as examples of how to write Ansible roles #
+####################################################################
+
+- name: Attempt to install dependencies for OpenSSH > 7.8
+  block:
+    - name: Ensure bcrypt 3.1.5 available
+      become: true
+      pip:
+        name: bcrypt==3.1.5
+        extra_args: "-c {{ remote_constraints }}"
+
+    - name: Register bcrypt version
+      command: "{{ ansible_python.executable }} -c 'import bcrypt; print(bcrypt.__version__)'"
+      register: bcrypt_version
+  ignore_errors: true
+
+- name: Ensure bcrypt_version is defined
+  set_fact:
+    bcrypt_version:
+      stdout: 0.0
+  when: bcrypt_version is not defined

tests/integration/targets/openssh_keypair/tests/validate.yml

@@ -138,3 +138,31 @@
   assert:
     that:
       - privatekey8_result_force is changed
+
+- block:
+    - name: Check that password protected key with passphrase was regenerated
+      assert:
+        that:
+          - privatekey9_modified_result is changed
+
+    - name: Check that modifying unprotected key with passphrase fails
+      assert:
+        that:
+          - privatekey10_result is failed
+          - "'Unable to read the key. The key is protected with a passphrase or broken.' in privatekey8_result.msg"
+
+    - name: Check that unprotected key was regenerated with force=yes and passphrase supplied
+      assert:
+        that:
+          - privatekey10_result_force is changed
+
+    - name: Check that ssh-keygen output from passphrase protected key matches openssh_keypair
+      assert:
+        that:
+          - privatekey10_result_force.public_key == privatekey10_result_sshkeygen.stdout
+
+    - name: Check that PEM encoded private keys are loaded successfully
+      assert:
+        that:
+          - privatekey11_result is success
+  when: cryptography_version.stdout is version('3.0', '>=') and bcrypt_version.stdout is version('3.1.5', '>=')

tests/integration/targets/openssh_keypair/vars/main.yml

@@ -1,4 +1,5 @@
 ---
+passphrase: password
 regenerate_values:
   - never
   - fail